The purpose of this study was to examine transfer high schools within the New York City Department of Education (NYCDOE) and the instructional cultures developed by their principals. Transfer high schools reengage students who were previously truant and at risk of discontinuing their education. Four NYCDOE transfer high schools were studied through a multisite case study methodology. For each school, the principal participated in a semi-structured interview with the researcher, and a group of two to three teachers participated in a focus group interview. Additionally, a document review was conducted. The use of three types of data collection allowed for triangulation. The interview transcripts were reviewed for themes through a coding process, and the themes, which included the need for youth development and social justice, became the structure for the study's findings. The results indicated that principals use a wide-range of systems and structures to support their teachers in meeting the instructional focus of their schools. The results also indicated that principals felt isolated and unsupported despite the presence of systems for collaboration. Recommendations include providing teachers with more training in the principles of youth development and social justice as well as providing principals with more support. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]